Pep Guardiola is possibly the greatest tactical mind of his generation. But he still hasn’t quite got to grips with the Champions League, has he?

For all the countless leagues and domestic cups he’s added to his personal trophy cabinet over the years, his European Cup count stands at just two: and they are both firmly in the past.

In his spells at Bayern Munich and Manchester City, he has never been able to go all the way in Europe. There is always something that stops him, and at the root of it is a tendency to overthink his game-plan for the now-or-never ties.

Their defeat to Chelsea in the 2021 final is the most recent example of that, but we’ve taken a look back at his track record over the years and some of the games where Pep-ball went a little bit too far.

You could argue that this one was more Jose Mourinho out-thinking Pep than Pep out-thinking Pep, but either way, there were some real blunders from Guardiola in the 2010 semi-final.

While Mourinho’s Inter were a well-drilled unit of functional sh**houses on their way to European glory, Guardiola’s team were all about playing football the ‚right‘ way…but it didn’t work on this occasion.

The decision to play Lionel Messi in a free role off the left-flank, where he was almost completely isolated, was bewildering. As was Barça’s bizarre tendency to squeeze the middle of the pitch when Inter had the ball, resulting in Maicon having one of the games of his life down the right.

Pep’s tenure at Barça was coming to an end by 2012, but having lost the first leg of the semi final 1-0 at Stamford Bridge, he still felt he had one more shot at glory in the tank.

His decision to set Barça up in a 3-4-3, with Isaac Cuenca and Andres Iniesta as wing-backs, initially looked to be working as they raced into a 2-0 lead at Camp Nou.

But the house of cards eventually came crashing down, as Chelsea – down to ten men thanks to John Terry’s red card – came roaring back. They sealed their spot in the final thanks to Ramires‘ strike and Fernando Torres‘ most famous goal in blue, going on to be crowned champions of Europe.

Guardiola’s non-negotiable philosophy of tiki-taka football always seemed like a square peg in a round hole at Bayern Munich. Even though it led them to three successive Bundesligas, it was never really a good fit, and that was exposed in brutal terms by Real Madrid in his first season.

It was clear what Bayern’s strengths were, with the pace and direct running of Arjen Robben and Franck Ribery playing ahead of the industrious engine room of Toni Kroos and Bastian Schweinsteiger.

But Pep refused to play to them, and the result was a 5-0 aggregate defeat – which included a humbling 4-0 demolition at the Allianz.

Kylian Mbappe. Fabinho. Bernardo Silva. Thomas Lemar. Benjamin Mendy.

The Monaco team City faced in the 2017 quarter-finals looks ridiculously good in hindsight, but it seemed as if they were heading for the exit door after City came back from 3-2 down to win 5-3 at the Etihad.

For the second leg, though, Guardiola sprung some surprises. Surprises like Aleksandar Kolarov starting at centre-back despite Nicolas Otamendi being fit and on the bench.

Tiemoue Bakayoko’s late strike eventually sealed their fate in one of the Champions League’s all time classics, as Monaco advanced on away goals after six goals apiece.

Guardiola needed a miracle at the Etihad in this one, after Liverpool’s 3-0 victory at Anfield had put his seemingly invincible team on the brink of elimination.

Naturally, he went gung-ho for the second leg, but seemed to forget that defending was still important. Nicolas Otamendi, Aymeric Laporte and Kyle Walker were the only defenders named in the starting lineup, and there was no rhyme nor reason to their shape at the back as they chased the impossible dream.

To be fair, had it not been for a very dodgy offside call against Leroy Sane, this one might have panned out differently. But City’s lack of defensive discipline ultimately cost them as Liverpool came from behind on the night to win the tie 5-1.

The second leg of this one, as City won 4-3 only to crash out on away goals, will always be remembered as one of the best ever. But it’s worth remembering why that game was so good.

City had to go for it at the Etihad because, once again, they had left themselves a lot to do. Guardiola’s decision to start Fabian Delph at left-back up against Son Heung-min was perplexing, while Kevin De Bruyne was left on the bench until the 89th minute – despite City desperately struggling to create.

It set up one of the best Champions League games ever, but it ultimately cost City a semi-final place.

The 2019/20 season was a difficult one for City. After losing their league title to Liverpool, they could really have done with a sustained run in the Champions League, and a one-off quarter final tie with Lyon presented them with a good opportunity to do just that.

So when the team-sheet came out and it didn’t have David Silva, Bernardo Silva or Riyad Mahrez on it, fans were a little bit confused as to what Guardiola was trying to do.

That confusion turned into blind rage when Guardiola persisted with an awkward back five for the entirety of the game, without using a single substitute, and Moussa Dembele went on to seal a memorable 3-1 victory for Lyon.

And now for the big one. After finally ending their semi-final curse against PSG and booking their flight to Istanbul (or Porto, as it turned out), this was supposed to be the one where Guardiola’s City finally took that last step and crowned themselves champions of Europe.

But they came up against a Chelsea team who were organised, well-drilled, and had the quality to punish them.

Chelsea had the beating of City in almost every area in this one, but what decidedly did not help was Guardiola’s big decision not to play a defensive midfielder. The trio of Phil Foden, Bernardo Silva and Ilkay Gundogan were far too passive and lightweight, and by the time Pep saw sense and threw on Fernandinho, it was too little, too late.